CN114023573B - Preparation method of triazinyl aza two-dimensional electrode material - Google Patents
Preparation method of triazinyl aza two-dimensional electrode material Download PDFInfo
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- CN114023573B CN114023573B CN202111287011.9A CN202111287011A CN114023573B CN 114023573 B CN114023573 B CN 114023573B CN 202111287011 A CN202111287011 A CN 202111287011A CN 114023573 B CN114023573 B CN 114023573B
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- electrode material
- triazinyl
- aza
- phenylenediamine
- nitrogen
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- 239000007772 electrode material Substances 0.000 title claims abstract description 24
- 238000002360 preparation method Methods 0.000 title claims abstract description 8
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract description 36
- 229960000892 attapulgite Drugs 0.000 claims abstract description 22
- 229910052625 palygorskite Inorganic materials 0.000 claims abstract description 22
- CBCKQZAAMUWICA-UHFFFAOYSA-N 1,4-phenylenediamine Chemical compound NC1=CC=C(N)C=C1 CBCKQZAAMUWICA-UHFFFAOYSA-N 0.000 claims abstract description 18
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 18
- 239000000463 material Substances 0.000 claims abstract description 13
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical compound OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 claims abstract description 10
- 239000002262 Schiff base Substances 0.000 claims abstract description 8
- 150000004753 Schiff bases Chemical class 0.000 claims abstract description 8
- 238000006243 chemical reaction Methods 0.000 claims abstract description 8
- 230000002194 synthesizing effect Effects 0.000 claims abstract description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 19
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 14
- 238000003756 stirring Methods 0.000 claims description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 8
- 238000002156 mixing Methods 0.000 claims description 7
- 239000000203 mixture Substances 0.000 claims description 7
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 6
- 238000001035 drying Methods 0.000 claims description 6
- 229910052740 iodine Inorganic materials 0.000 claims description 6
- 239000011630 iodine Substances 0.000 claims description 6
- 238000000034 method Methods 0.000 claims description 6
- 238000000967 suction filtration Methods 0.000 claims description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 3
- 239000011521 glass Substances 0.000 claims description 3
- 238000010438 heat treatment Methods 0.000 claims description 3
- 239000005457 ice water Substances 0.000 claims description 3
- 238000001953 recrystallisation Methods 0.000 claims description 3
- 238000010992 reflux Methods 0.000 claims description 3
- 238000000926 separation method Methods 0.000 claims description 3
- 239000002904 solvent Substances 0.000 claims description 3
- 239000000126 substance Substances 0.000 claims description 3
- 230000001939 inductive effect Effects 0.000 claims description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 abstract description 10
- 229910021389 graphene Inorganic materials 0.000 abstract description 8
- 239000010405 anode material Substances 0.000 abstract description 3
- 230000009286 beneficial effect Effects 0.000 abstract description 3
- 230000008602 contraction Effects 0.000 abstract description 2
- 125000005842 heteroatom Chemical group 0.000 abstract description 2
- 150000002500 ions Chemical class 0.000 abstract description 2
- 239000000047 product Substances 0.000 description 9
- 238000000862 absorption spectrum Methods 0.000 description 4
- 235000019441 ethanol Nutrition 0.000 description 4
- HBBGRARXTFLTSG-UHFFFAOYSA-N Lithium ion Chemical compound [Li+] HBBGRARXTFLTSG-UHFFFAOYSA-N 0.000 description 3
- 238000010521 absorption reaction Methods 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 238000010306 acid treatment Methods 0.000 description 3
- 238000011161 development Methods 0.000 description 3
- 229910001416 lithium ion Inorganic materials 0.000 description 3
- 239000007773 negative electrode material Substances 0.000 description 3
- 229920000767 polyaniline Polymers 0.000 description 3
- 239000004927 clay Substances 0.000 description 2
- 229920001940 conductive polymer Polymers 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- -1 transition metal sulfide Chemical class 0.000 description 2
- 229910052582 BN Inorganic materials 0.000 description 1
- PZNSFCLAULLKQX-UHFFFAOYSA-N Boron nitride Chemical compound N#B PZNSFCLAULLKQX-UHFFFAOYSA-N 0.000 description 1
- 238000005411 Van der Waals force Methods 0.000 description 1
- 238000004220 aggregation Methods 0.000 description 1
- 230000002776 aggregation Effects 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 229910002804 graphite Inorganic materials 0.000 description 1
- 239000010439 graphite Substances 0.000 description 1
- 238000009396 hybridization Methods 0.000 description 1
- GKTNLYAAZKKMTQ-UHFFFAOYSA-N n-[bis(dimethylamino)phosphinimyl]-n-methylmethanamine Chemical compound CN(C)P(=N)(N(C)C)N(C)C GKTNLYAAZKKMTQ-UHFFFAOYSA-N 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000033116 oxidation-reduction process Effects 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 238000012827 research and development Methods 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
Classifications
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- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01G—CAPACITORS; CAPACITORS, RECTIFIERS, DETECTORS, SWITCHING DEVICES, LIGHT-SENSITIVE OR TEMPERATURE-SENSITIVE DEVICES OF THE ELECTROLYTIC TYPE
- H01G11/00—Hybrid capacitors, i.e. capacitors having different positive and negative electrodes; Electric double-layer [EDL] capacitors; Processes for the manufacture thereof or of parts thereof
- H01G11/84—Processes for the manufacture of hybrid or EDL capacitors, or components thereof
- H01G11/86—Processes for the manufacture of hybrid or EDL capacitors, or components thereof specially adapted for electrodes
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
- C08G73/02—Polyamines
- C08G73/0273—Polyamines containing heterocyclic moieties in the main chain
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01G—CAPACITORS; CAPACITORS, RECTIFIERS, DETECTORS, SWITCHING DEVICES, LIGHT-SENSITIVE OR TEMPERATURE-SENSITIVE DEVICES OF THE ELECTROLYTIC TYPE
- H01G11/00—Hybrid capacitors, i.e. capacitors having different positive and negative electrodes; Electric double-layer [EDL] capacitors; Processes for the manufacture thereof or of parts thereof
- H01G11/22—Electrodes
- H01G11/26—Electrodes characterised by their structure, e.g. multi-layered, porosity or surface features
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01M—PROCESSES OR MEANS, e.g. BATTERIES, FOR THE DIRECT CONVERSION OF CHEMICAL ENERGY INTO ELECTRICAL ENERGY
- H01M10/00—Secondary cells; Manufacture thereof
- H01M10/05—Accumulators with non-aqueous electrolyte
- H01M10/052—Li-accumulators
- H01M10/0525—Rocking-chair batteries, i.e. batteries with lithium insertion or intercalation in both electrodes; Lithium-ion batteries
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- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01M—PROCESSES OR MEANS, e.g. BATTERIES, FOR THE DIRECT CONVERSION OF CHEMICAL ENERGY INTO ELECTRICAL ENERGY
- H01M4/00—Electrodes
- H01M4/02—Electrodes composed of, or comprising, active material
- H01M4/36—Selection of substances as active materials, active masses, active liquids
- H01M4/60—Selection of substances as active materials, active masses, active liquids of organic compounds
- H01M4/602—Polymers
- H01M4/606—Polymers containing aromatic main chain polymers
- H01M4/608—Polymers containing aromatic main chain polymers containing heterocyclic rings
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- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01M—PROCESSES OR MEANS, e.g. BATTERIES, FOR THE DIRECT CONVERSION OF CHEMICAL ENERGY INTO ELECTRICAL ENERGY
- H01M4/00—Electrodes
- H01M4/02—Electrodes composed of, or comprising, active material
- H01M2004/026—Electrodes composed of, or comprising, active material characterised by the polarity
- H01M2004/027—Negative electrodes
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
- Y02E60/00—Enabling technologies; Technologies with a potential or indirect contribution to GHG emissions mitigation
- Y02E60/10—Energy storage using batteries
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- Manufacturing & Machinery (AREA)
- Microelectronics & Electronic Packaging (AREA)
- General Chemical & Material Sciences (AREA)
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- Health & Medical Sciences (AREA)
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- Medicinal Chemistry (AREA)
- Battery Electrode And Active Subsutance (AREA)
Abstract
The invention relates to a preparation method of a triazinyl aza two-dimensional electrode material, which comprises the steps of firstly synthesizing a nitrogen-rich material by utilizing Schiff Base reaction of p-phenylenediamine and cyanuric acid; and then, the synthesized nitrogen-rich material is induced into a two-dimensional structure by using attapulgite, so that the nitrogen-rich material with a two-dimensional plane structure is obtained. The nitrogen-rich electrode material with the two-dimensional plane structure is rich in heteroatoms, has high specific capacitance and large specific surface area, is of a porous structure, is beneficial to the entry and exit of ions, can stabilize the structure during expansion or contraction, is not easy to collapse, has good stability, and can replace graphene to be used as a good anode material.
Description
Technical Field
The invention relates to a preparation method of a triazinyl aza two-dimensional electrode material. Belonging to the technical field of battery electrode materials.
Background
The performance of lithium ion batteries depends largely on the negative electrode material, and the existing commercial lithium ion battery negative electrode uses graphite carbon as the negative electrode material, so that the lower theoretical capacity of the lithium ion battery negative electrode can not adapt to the development of related industries. Therefore, development of a negative electrode material having low cost and high performance is one of the main contents at present.
Graphene is the thinnest two-dimensional material discovered at present, has a unique crystal structure, a rich C hybridization structure and interface performance, and shows excellent electrochemical properties. For example, a high specific surface area, excellent conductivity at room temperature, and stable electrochemical properties. However, strong van der Waals force exists between graphene sheets, so that aggregation is easy to generate, and the graphene sheets are difficult to dissolve in water and common organic solvents, so that application research and development of the graphene sheets are limited. Therefore, the development of novel graphene-like two-dimensional crystal materials with special properties becomes a research hotspot, such as monoatomic layer hexagonal boron nitride, transition metal sulfide, phosphazene, borazene and the like.
Polyaniline is considered to be the most promising conductive polymer for application in supercapacitor electrode materials, with many excellent properties. For example, polyaniline has various oxidation-reduction states, has the largest theoretical pseudocapacitance in a plurality of conductive polymers, has good stability and is easy to synthesize and process, and the polyaniline has higher conductivity after being doped, so that the conduction rate of electrons in the charge and discharge process is greatly improved.
Disclosure of Invention
The invention provides a graphene-like electrode material capable of replacing graphene in order to solve the problems in the prior art.
In order to achieve the above purpose, the technical scheme provided by the invention is as follows: a preparation method of a triazinyl aza two-dimensional electrode material comprises the following steps:
firstly, synthesizing a nitrogen-rich material by utilizing Schiff Base reaction of p-phenylenediamine and cyanuric acid;
and secondly, inducing the synthesized nitrogen-rich material into a two-dimensional structure by using attapulgite to obtain the triazinyl aza two-dimensional electrode material.
The technical scheme is further designed as follows: in the first step, p-phenylenediamine and iodine are mixed in an ethanol solvent, and the treated p-phenylenediamine is obtained for standby by adopting ice-water bath and stirring for 30 min;
and then mixing the treated p-phenylenediamine and cyanuric acid in a toluene solvent, carrying out Schiff Base reaction under the heating of an oil bath, and refluxing for 8 hours to obtain a nitrogen-rich material mixture.
In the first step, the mass ratio of p-phenylenediamine to iodine is 1:2.
in the first step, the mass ratio of the p-phenylenediamine to the cyanuric acid substance is 2:3.
in the second step, firstly mixing and stirring the attapulgite with 1mol/L hydrochloric acid for 30min, and obtaining dry attapulgite after suction filtration;
adding the dry attapulgite into the nitrogen-rich material mixture obtained in the step one, connecting a glass water separator for water separation, carrying out suction filtration, recrystallizing with ethanol, and drying;
finally, hydrochloric acid is added into the dried product, stirring is carried out for 8 hours, attapulgite therein is dissolved, and the final product-triazinyl aza two-dimensional electrode material is obtained.
Absolute ethanol is used for recrystallization.
The invention has the beneficial effects that:
the product of the invention is a graphene-like material which can replace graphene, the cost can be effectively reduced by synthesizing the anode material by a chemical method, and the synthesis method of the material does not generate a large amount of waste, thereby protecting the environment. The nitrogen-rich electrode material with the two-dimensional plane structure is rich in heteroatoms, has high specific capacitance and large specific surface area, is of a porous structure, is beneficial to the entry and exit of ions, can stabilize the structure during expansion or contraction, is not easy to collapse, has good stability, and can replace graphene to be used as a good anode material.
Drawings
FIG. 1 is a reaction scheme of a preparation process of a triazinyl aza two-dimensional electrode material according to the present invention;
FIG. 2 is a chart showing the IR absorption spectrum I of the electrode material according to the present embodiment;
fig. 3 is a second infrared absorption spectrum of the electrode material prepared in this example.
Detailed Description
The invention will now be described in detail with reference to the accompanying drawings and specific examples.
Examples
The preparation method of the nitrogen-rich electrode material with the two-dimensional planar structure comprises the following steps:
step one, synthesizing a nitrogen-rich material by utilizing a Schiff Base reaction;
1.1, mixing p-phenylenediamine and iodine in an ethanol solvent, and stirring for 30min for later use by adopting an ice-water bath, wherein the mass ratio of the p-phenylenediamine to the iodine is 1:2;
1.2, mixing the treated p-phenylenediamine and cyanuric acid in toluene solvent, wherein the mass ratio of the p-phenylenediamine to the cyanuric acid is 2:3, carrying out Schiff Base reaction on the mixture under the heating of an oil bath at 90 ℃ and refluxing for 8 hours to obtain a nitrogen-rich material mixture.
Step two, utilizing attapulgite clay to induce the synthesized nitrogen-rich material into a two-dimensional structure;
2.1, mixing and stirring attapulgite with 1mol/L hydrochloric acid for 30min, and carrying out suction filtration to obtain dry attapulgite for later use; the dosage of the attapulgite is larger than that of the p-phenylenediamine and cyanuric acid;
2.2, adding the dry attapulgite into the nitrogen-rich material mixture obtained in the step one, connecting a glass water separator for water separation at the temperature of 115 ℃, carrying out suction filtration, recrystallizing with ethanol, and carrying out drying treatment;
and 2.3, finally adding acid into the dried product, stirring for 8 hours, and dissolving the attapulgite therein to obtain the final product-triazinyl aza two-dimensional electrode material.
In this example, three acid solutions were used to dissolve the attapulgite clay, respectively, with the following results:
acid treatment 1: 1.2g of the dried crude product was taken in a beaker, a 20% HF solution was added to the product, stirred for 8 hours, the attapulgite was dissolved, and after drying, 0.29g was weighed.
Acid treatment 2: 1.2g of the dried crude product was taken in a beaker, 36.8% hydrochloric acid solution was added to the product, stirred for 8 hours, the attapulgite was dissolved, and after drying, 0.81g was weighed.
Acid treatment 3: taking 0.15 dry coarse product in a beaker, adding 5% hydrochloric acid solution into the product, stirring for 8 hours, dissolving attapulgite, and weighing to 0.15g after drying. From the above examples, it is evident that the removal of attapulgite in HF solution is more complete.
The Schiff base product is easy to hydrolyze into the original aldehyde ketone under the catalysis of acid in the presence of water, so that the experiment is carried out under anhydrous condition, and absolute ethyl alcohol is used for recrystallization.
Two parts of the electrode material prepared in this example were respectively taken for infrared absorption spectrum analysis, and the infrared absorption spectra are respectively shown in fig. 2 and 3, and it can be seen that: the product was found to be 3422, 3535cm -1 Absorption peak with N-H bond at 1645cm -1 An absorption peak with a C=N bond at 1720cm -1 The c=0 bond absorption peak at this point disappeared and the two reactants at the surface had been attached.
The technical scheme of the invention is not limited to the embodiments, and all technical schemes obtained by adopting equivalent substitution modes fall within the scope of the invention.
Claims (4)
1. The preparation method of the triazinyl aza two-dimensional electrode material is characterized by comprising the following steps:
firstly, synthesizing a nitrogen-rich material by utilizing Schiff Base reaction of p-phenylenediamine and cyanuric acid;
inducing the synthesized nitrogen-rich material into a two-dimensional structure by using attapulgite to obtain a triazinyl aza two-dimensional electrode material;
in the second step, firstly mixing and stirring the attapulgite with 1mol/L hydrochloric acid for 30min, and obtaining dry attapulgite after suction filtration;
adding the dry attapulgite into the nitrogen-rich material mixture obtained in the step one, connecting a glass water separator for water separation, carrying out suction filtration, recrystallizing with ethanol, and drying;
finally, hydrochloric acid is added into the dried product, stirring is carried out for 8 hours, attapulgite therein is dissolved, and the final product-triazinyl aza two-dimensional electrode material is obtained;
absolute ethanol is used for recrystallization.
2. The method for preparing the triazinyl aza two-dimensional electrode material according to claim 1, wherein:
in the first step, p-phenylenediamine and iodine are mixed in an ethanol solvent, and the treated p-phenylenediamine is obtained for standby by adopting ice-water bath and stirring for 30 min;
and then mixing the treated p-phenylenediamine and cyanuric acid in a toluene solvent, carrying out Schiff Base reaction under the heating of an oil bath, and refluxing for 8 hours to obtain a nitrogen-rich material mixture.
3. The method for preparing the triazinyl aza two-dimensional electrode material according to claim 2, wherein: in the first step, the mass ratio of p-phenylenediamine to iodine is 1:2.
4. a method of preparing a triazinyl aza two-dimensional electrode material according to claim 3, characterized in that: in the first step, the mass ratio of the p-phenylenediamine to the cyanuric acid substance is 2:3.
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| CN202111287011.9A CN114023573B (en) | 2021-11-02 | 2021-11-02 | Preparation method of triazinyl aza two-dimensional electrode material |
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Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105185963A (en) * | 2015-09-08 | 2015-12-23 | 湖北工程学院 | High-performance nitrogen-rich carbon composite electrode material and preparation method thereof |
| CN107098910A (en) * | 2017-04-12 | 2017-08-29 | 中国科学院青岛生物能源与过程研究所 | A kind of rich carbon two-dimensional material of new triazine and preparation method thereof |
| CN108584944A (en) * | 2018-06-26 | 2018-09-28 | 北京化工大学 | A kind of preparation method of the ultracapacitor rich nitrogen grading porous carbon electrode material of high-specific surface area |
| CN110090633A (en) * | 2019-06-04 | 2019-08-06 | 东华理工大学 | A kind of super cross-linked porous polymer material and its preparation method and application of richness nitrogen |
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2021
- 2021-11-02 CN CN202111287011.9A patent/CN114023573B/en active Active
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105185963A (en) * | 2015-09-08 | 2015-12-23 | 湖北工程学院 | High-performance nitrogen-rich carbon composite electrode material and preparation method thereof |
| CN107098910A (en) * | 2017-04-12 | 2017-08-29 | 中国科学院青岛生物能源与过程研究所 | A kind of rich carbon two-dimensional material of new triazine and preparation method thereof |
| CN108584944A (en) * | 2018-06-26 | 2018-09-28 | 北京化工大学 | A kind of preparation method of the ultracapacitor rich nitrogen grading porous carbon electrode material of high-specific surface area |
| CN110090633A (en) * | 2019-06-04 | 2019-08-06 | 东华理工大学 | A kind of super cross-linked porous polymer material and its preparation method and application of richness nitrogen |
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